KR101345571B1 - Herbicidal composition - Google Patents

Abstract

As active ingredient, N- (7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxadin-6-yl) cyclohex-1 A herbicidal composition comprising ene-1,2-dicarboxamide (flumioxazine) and a compound of formula 1 in a weight ratio of 1: 0.01 to 1: 100 to inhibit weeds in cropland, vegetable gardens, trees or non-cultivated land. Has good herbicidal activity and does not cause harm to useful plants.

Formula 1

Herbicidal composition, flumioxazine, herbicidal activity, weak

Description

Herbicidal composition [0001]

The present invention relates to herbicidal compositions and herbicidal methods.

Currently, many herbicides are commercially available, and they are widely used. However, the weeds to be suppressed are diverse and growing over time. For this reason, there is a need for herbicides having high herbicidal activity, a broad range of weed suppression, long term effects and safety against crops.

The present invention provides compositions and methods for inhibiting a variety of weeds, with no harm to crops and having a high herbicidal effect.

In other words, the present invention provides the active ingredient N- (7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxadin-6-yl ) Is a herbicidal composition comprising cyclohex-1-ene-1,2-dicarboxamide (flumioxazine) and a compound of formula (1) in a weight ratio of 1: 0.01 to 1: 100.

The present invention also provides a method of weeding, comprising applying flumioxazine and a compound of formula 1 in a weight ratio of 1: 0.01 to 1: 100 to the weeds or to the soil where the weeds will grow or grow.

Flumioxazine [chemical name: N- (7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxadin-6-yl) cyclohex -1-ene-1,2-dicarboxamide] is described in Crop Protection Handbook Vol. 89 (2003), Meister Publishing Company, ISBN: 1-892829-06-1, page C-236. It can be prepared by known production methods, and formulations containing flumioxazine are commercially available.

Compounds of formula 1 can be prepared by known methods of preparation described in USP 2005-0032650A.

The herbicidal composition of the present invention comprises flumioxazine and the compound of formula 1 as an active ingredient, and the weight ratio of flumioxazine: compound of formula 1 in the herbicidal composition of the present invention is 1: 0.01 to 1: 100, preferably 1 : 0.1 to 1:20, more preferably 1: 0.2 to 1:10.

The herbicidal compositions of the present invention have herbicidal activity against various types of weeds, and thus can be used to effectively inhibit various types of weeds in areas, vegetable gardens, trees or non-cultivated land where crops are grown with or without cultivation techniques. Can be. In addition, it does not cause significant harm to useful plants.

The present invention also provides 1: 0.01 to 1: 100, preferably 1: 0.1 to 1:20, more preferably in the weeds or in the soil of the place where weeds are to be grown, simultaneously or simultaneously with the flumioxazine and the compound of the formula (1). Preferably we provide a method of inhibiting weeds, including applying in a weight ratio of 1: 0.2 to 1:10.

The method of the present invention can be used to inhibit weeds, especially in cropland, vegetable gardens, trees or non-cultivated land.

Examples of farmland in the present invention include food crops such as peanuts, soybeans, corn, wheat and barley; Grasses such as sorghum and oats; Industrial crops such as cotton; And plantations of sugar crops such as sugar cane. Examples of vegetable gardens in the present invention include Solanaceae vegetables, such as eggplant, tomatoes, bell peppers, peppers, and potatoes; Cucurbitaceae vegetables such as cucumbers, pumpkins, zucchini, watermelons and melons; Mustard vegetables such as radishes, turnips, horseradish, caliber cabbage, Chinese cabbage, cabbage, freshly, broccoli and cauliflower; Compositae vegetables such as burdock, garland chrysanthemum, artichoke and lettuce; Liliaceae vegetables such as leek, onion, garlic and asparagus; Umbelliferae vegetables such as carrots, parsley, celery and parsnips; Chenopodiaceae vegetables such as spinach and chard; Lamiacea vegetables such as perilla, mint, wild grass and lavender; Strawberry; sweet potato; yam; And cultivation of taro toran. Examples of arbors include orchards, tea plantations, mulberry fields, coffee plantations, banana plantations, palm plantations, flower fields, flower fields, seedlings, seedlings, forests and gardens. Examples of orchards include fruit fruits such as apples, pears, Japanese pears, Chinese quince and quince; Nucleus, for example peach, prune, nectarine, Japanese apricot, cherry, apricot and prune; Citrus fruits such as Satsuma orange, oranges, lemons, limes and grapefruits; Nuts such as chestnuts, walnuts, hazel, almonds, pistachios, cashews and macadamia nuts; Berries, such as blueberries, vineberries, blackberries and raspberries; grape; Persimmon tree; olive; And loquat. Examples of non-arable land in the present invention include playgrounds, vacant lands, railways, parks, parking lots, roads, riverbeds, sub-transmission sites, residential and factory sites.

Examples of weeds include:

Polygonaceae weeds, for example Polygonum convolvulus (wild buckwheat), Polygonum lapathifolium (white), Polygonum pensylvanicum (Pennsylvania) Willow), Polygonum persicaria (springtime), Rumex crispus ( Russian ), Rumex obtusifolius (European dock) And Polygonum cuspidatum ( J. Keun- Geun);

Purslane and weeds, for example Portulaca oleracea (purslane);

Caryophyllaceae weeds, for example Stellaria media (starflower);

Chenopodiaceae weeds, for example, Chenopodium album (white mist) and Kochia scoparia (pink needle);

Amaranthaceae weeds, for example Amaranthus retroflexus (Hermal) and Amaranthus hybridus (Amaranth);

Crusiferae weeds, for example Raphanus raphanistrum ( wifi ), Sinapis arvensis (wildcat) and Capsella bursa-pastoris (Cress);

Leguminosae weeds, for example Sesbania exaltata (hemp sesbania), Cassia obtusifolia (sicklepod), Desmodium Tortu Desmodium tortuosum (Florida beggarweed), Trifolium repens (white flower clover), Pueraria lobata (칡), and Vicia angustifolia ( salk) );

Malvaceae weeds, for example Abutilon theophrasti (tab) and Sida spinosa (prickly sida);

Violaceae weeds such as Viola arvensis (wild pansy) and Viola tricolor (wild pansy);

Rubiaceae weeds, for example Galium aparine (cleavers);

Convolvulaceae weeds, for example Ipomoea hederacea ( Ipomoea ), Ipomoea purpurea (tall morning glory), Ipomoea hederacea bar Ipomoea hederacea var integriuscula ( Ipomoea Morning Glory), Ipomoea lacunose ( Tangled Morning Glory) and Convolvulus arvensis (Western Messace);

Lamitae weeds, such as Lamium purpureum (often herbaceous ) and Lamium amplexicaule (clown sprouts);

Solanaceae weeds, for example Datura stramonium (alcohol) and Solanum nigrum (black paper);

Scrophulariaceae weeds, for example Veronica persica (larvae) and Veronica hederaefolia (ivy leaf tail grass);

Compositae weeds, for example Xanthium pensylvanicum (Docktail), Helianthus annuus (Sunflower), Matricaria inodora (Flower Weasel ) Artemisia), Creative Sante drought harder Tomb (chrysanthemum segetum) (peacock chrysanthemum), Mart Rica Leah Mart Rica riohyi death (Matricaria matricarioides) (Weasel wormwood), Ambrosia Artemisia misiyi polyamic (Ambrosia artemisiifolia) (ragweed) Ambrosia tree in the blood ( Ambrosia trifida (foliar leaf), Erigeron Canadensis (Rawtail Forget), Artemisia princes (Japanese mugwort), and Solidago altissima ( Thick Seaweed);

Boraginaceae weeds, for example Myosotis arvensis (forget-me-not);

Asclepiadaceae weeds, for example Asclepias syriaca (quarium);

Euphorbiaceae weeds, for example Euphorbia helioscopia (lighthouse) and Euphorbia maculata (silkweed);

Geraniaceae weeds, for example Geranium carolinense (US ratus) and Erodium cicutarium ;

Gramineae weeds, for example Echinochloa crus-galli (Dolpi) , Setaria viridis ( puppy), Setaria faberi (Autumn ) Foxtail), Digitaria sanguinalis (southern crabgrass), Eleusine indica ( rakeh ), Poa annua (sapourea), Allopecurus miyo Alopecurus myosuroides (western grass), Avena fatus (wild oats), Sorghum halepense (Johnsongrass), Agropyron repens (wheat wheat) ), Bromus tectorum (downy brome), Cynodone dactylon ( Usangrass ), Panicum dichotomiflorum (American dog), Panicum Panicum texanum (Texas panicum, Sorghum vulgare ) (shattercane) and Lolium multiflorum (jumbo);

Chicken jangpul weeds (Commelinaceae weeds), for example, comb Melina kommu varnish (Commelina communis) (Tradescantia) and comb Melina Bengal alkylene sheath (Commelina benghalensis) (Bengal often Tradescantia (Bengal dayflower));

Equisetaceae weeds, for example Equisetum arvense (horsetail); And

Cyperaceae weeds, for example Cyperus iria (combatants), Cyperus rotundus (hyangbu) and Cyperus esculentus (oil bone ) ).

The herbicidal compositions of the present invention may be formulated into emulsifiable concentrates, wettable powders, suspending concentrates, granules and the like by mixing with solid or liquid carriers and, optionally, surfactants and other auxiliaries for formulation. These formulations generally contain about 0.1 to 90% by weight, preferably about 1 to 80% by weight of the total amount of flumioxazine and the compound of formula (1).

Examples of solid carriers used to formulate the compositions of the present invention include fine powders and granules of clay, for example kaolin, diatomaceous earth, hydrated synthetic silica, Fuvasami clay, bentonite and terra alba Fine powder and granules; talc; Other inorganic minerals such as sericite, quartz powder, sulfur powder, activated carbon and calcium carbonate; And chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride and urea. Examples of liquid carriers include water; Alcohols such as methanol and ethanol; Ketones such as acetone, methyl ethyl ketone and cyclohexanone; Aromatic hydrocarbons such as toluene, xylene, ethylbenzene and methylnaphthalene; Non-aromatic hydrocarbons such as hexane, cyclohexane and kerosene; Esters such as ethyl acetate and butyl acetate; Nitriles such as acetonitrile and isobutyronitrile; Ethers such as dioxane and diisopropyl ether; Acid amides such as dimethylformamide and dimethylacetamide; Halogenated hydrocarbons such as dichloroethane and trichloroethylene.

Examples of surfactants used for formulation include alkyl sulfate esters, alkylsulfonate salts, alkylarylsulfonate salts, alkylaryl ethers, polyoxyethylene alkylaryl ethers, polyethylene glycol ethers, polyhydric alcohol esters and sugar alcohol derivatives. . Examples of other adjuvants for formulation include tackifiers and dispersants, such as casein; gelatin; Polysaccharides such as starch, gum arabic, cellulose derivatives, alginic acid; Lignin derivatives; Bentonite; And synthetic water soluble polymers such as polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid; And stabilizers such as PAP (isopropyl acid phosphate), BHT (2,6-tert-butyl-4-methylphenol), BHA (2- / 3-tert-butyl methoxy-4-methoxyphenol), Vegetable oils, mineral oils, fatty acids and fatty acid esters.

The herbicidal compositions of the present invention can also be prepared by formulating each of the active ingredients according to the above procedure and then mixing the respective formulations.

The obtained herbicidal composition can be applied to the herbicidal method of the present invention by itself. It can also be diluted with water or the like, after which the dilution can be applied to soil or plants. It may be expected that the herbicidal composition of the present invention will increase herbicidal effect by use with other herbicides. In addition, the herbicidal composition may be used in combination with insecticides, fungicides, plant growth regulators, fertilizers, softeners, soil improvers and the like.

The dosage or method of the herbicidal composition of the present invention depends on the mixing ratio of flumioxazine and the compound of formula 1 as the active ingredient, climatic conditions, formulation form, application time, application method, application place, target weeds and crops, It is generally about 1 to 1000 g of total active ingredient per ha. If the formulation is an emulsifiable concentrate, wettable powder, suspending concentrate, the desired amount is generally applied by dilution with about 100-2000 liters of water per ha. In addition, when the composition of the present invention is applied to weeds by foliar treatment, it is expected to increase the herbicidal effect on the weeds by adding an adjuvant to the dilution of the composition of the present invention.

Example

The invention is now described in detail by way of examples.

Formulation examples are provided below. In the following examples, part (s) means parts by weight (s).

Formulation Example 1

25 parts of flumioxazine, 25 parts of the compound of formula (1), 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 45 parts of hydrated synthetic silica are sufficiently ground and mixed to obtain a wettable powder.

Formulation Example 2

70 parts of flumioxazine, 14 parts of the compound of formula 1, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 11 parts of hydrated synthetic silica are sufficiently ground and mixed to obtain a wettable powder.

Formulation Example 3

14 parts of flumioxazine, 70 parts of the compound of formula 1, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 11 parts of hydrated synthetic silica are sufficiently ground and mixed to obtain a wettable powder.

Formulation Example 4

10 parts of flumioxazine, 5 parts of the compound of formula 1, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfate and 80 parts of hydrated synthetic silica are sufficiently ground and mixed to obtain a wettable powder.

Formulation Example 5

20 parts of flumioxazine, 20 parts of the compound of the formula (1), 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 54 parts of water are mixed and wet-pulverized to a particle diameter of 5 μm or less, and suspended in suspension. Obtain water.

Formulation Example 6

50 parts of flumioxazine, 10 parts of the compound of the formula (1), 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 34 parts of water were mixed, and wet-pulverized to a particle diameter of 5 μm or less, and suspended in suspension. Obtain water.

Formulation Example 7

5 parts of flumioxazine, 25 parts of the compound of the formula (1), 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 64 parts of water are mixed and wet-pulverized to a particle diameter of 5 μm or less, and suspended in suspension. Obtain water.

Formulation Example 8

4 parts of flumioxazine, 2 parts of the compound of formula (1), 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC (carboxymethylcellulose) and 88 parts of water are mixed and wet-pulverized to a particle diameter of 5 mu or less and concentrated to suspension. Obtain water.

Formulation Example 9

1 part of flumioxazine, 1 part of compound of Formula 1, Neocol YSK [sodium dialkylsulfosuccinate ester; Manufacturer: Daiichi Kogyo Seiyaku Co., Ltd.] 0.5 part, Toxanon GR31A [anionic polycarboxylate surfactant; Manufacturer: Sanyo Chemical Industries, Ltd. 2 parts, Kunigel V1 [bentonite; Manufacturer: Kuminime Industries Co., Ltd.] 30 parts and 65.5 parts of calcium carbonate are charged into a small kneader, mixed and kneaded and extruder [RG-5M; Manufacturer: Granulated with Kikusui Seisakusho, Ltd., fluid bed dryer [MDB-400; Manufacturer: Fuji Paudal Co., Ltd., and then filtered through 16 to 48 mesh to obtain granules.

Biological tests are provided below.

Evaluation standard

Herbicidal activity is assessed in 11 stages indicated by indicators 0 to 10, i.e., 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, with a grade of "0" treated plants observed No or little difference in growth between the and untreated plants, and a rating of "10" means that the test plants died completely or their growth was completely inhibited. The herbicidal values "7", "8", "9" and "10" indicate good herbicidal activity, and values below 6 indicate insufficient herbicidal activity. Damage to crops is assessed as "no damage", "slight", "medium" or "severe," "no damage" means no or little damage, and "slight" indicates that damage is weak. "Medium" means that the damage is moderate and "severe" means that severe damage is found.

Test Example 1

Plastic jars, 18 cm in diameter and 14 cm in height, were filled with field soil, and then wheat and peeling were planted. On the surface of the soil of the plastic complex described above, flumioxazine granules (granules containing 0.25% of flumioxazine; trade name: Broad Star, manufactured by Valent USA), a compound of formula (1) Granules (prepared using 1 part of a compound of formula 1, 0.5 parts of neocol YSK, 2 parts of toxanone GR31A, 30 parts of Kunigel V1 and 66.5 parts of calcium carbonate according to Formulation Example 9) and flumioxazine granules And a mixture of granules containing a compound of Formula 1 were manually applied in the amounts shown in Table 1.

Treated plants were grown in greenhouses. Herbicidal activity and damage to crops were tested 48 days after application. The results are shown in Table 1.

Test compound
Amount of active ingredient
(g / ha) Herbicide activity Weakness against crops Dolphin wheat Flumi Jade Photo 40 4 No damage The compound of formula (1)
50 0 No damage 100 2 No damage Plum Jade Photo +
The compound of formula (1) 40 + 50 7 No damage 40 + 100 10 No damage

As shown in Test Example 1, superior herbicidal effect was synergistically provided in the areas treated with the composition of the present invention, compared to the areas treated with flumioxazine or the compound of formula (1) alone. In addition, no damage was found in the wheat.

Test Example 2

Plastic jars 9 cm in diameter and 7 cm in height were filled with field soil, and then peanuts were planted. The next day, emulsifiable concentrate containing twinomixazine WDG (water dispersible granules containing 51% flumioxazine, trade name: Valor SX, manufactured by Valent U.S.) and a compound of formula (Twin) (Tween) 20 (surfactant, prepared by dissolving the compound of formula 1 in acetone containing sorbitan monolaurate polyglycol ether)] is diluted with a predetermined amount of water and the surface of the soil is Applied uniformly.

Treated plants were grown in greenhouses. Herbicidal activity and damage to crops were tested 21 days after application. The results are shown in Table 2.

Test compound
Amount of active ingredient (g / ha)
Weakness against crops peanut Plum Jade Photo +
The compound of formula (1)
25 + 50 No damage 50 + 50 No damage 100 + 100 No damage

As shown in Test Example 2, the compositions of the present invention caused little or no damage to peanuts.

Test Example 3

Plastic jars 32 cm wide, 22 cm deep, and 8 cm high were filled with field soil, and oil vines were planted. The next day, flumioxazine WDG (water dispersible granules containing 51% flumioxazine, trade name: Valor SX, manufactured by Valent U.S.), an emulsifiable concentrate containing the compound of formula (Twin) Prepared by dissolving a compound of formula 1 in acetone containing 20 (surfactant, sorbitan monolaurate polyglycol ether)] and mixtures thereof with a predetermined amount of water and using a small sprayer to homogenize the surface of the soil Applied.

Treated plants were grown in greenhouses. Herbicidal activity and damage to crops were tested 21 days after application. The results are shown in Table 3.

Test compound
Amount of active ingredient
(g / ha) Herbicide activity Oil Flumi Jade Photo
25 0 50 One The compound of formula (1) 100 7 Plum Jade Photo +
The compound of formula (1) 25 + 100 9 50 + 100 10

As shown in Test Example 3, superior herbicidal activity was synergistically provided in the areas treated with the compositions of the present invention as compared to areas treated with flumioxazine or the compound of formula (1) alone.

Test Example 4

Plastic jars 32 cm wide, 22 cm deep, and 8 cm high were filled with field soil, and then the tomatoes were transplanted, and the heads and hairs were planted. The next day, emulsifiable concentrate containing twinomixazine WDG (water dispersible granules containing 51% flumioxazine, trade name: Valor SX, manufactured by Valent U.S.) and a compound of formula (Twin) A mixture of 20 (surfactant, prepared by dissolving a compound of formula 1 in acetone containing sorbitan monolaurate polyglycol ether) was diluted with a predetermined amount of water and applied evenly to the surface of the soil with a small sprayer. .

Treated plants were grown in greenhouses. Herbicidal activity and damage to vegetables were tested 21 days after application. The results are shown in Table 4.

Test compound
Amount of active ingredient
(g / ha) Herbicide activity Weak against vegetables wire grass Hairy bean tomato Plum Jade Photo +
The compound of formula (1)




25 + 50 9 10 No damage 50 + 50 10 10 No damage 100 + 50 10 10 No damage 25 + 100 9 10 No damage 50 + 100 10 10 No damage 100 + 100 10 10 No damage 25 + 200 9 10 No damage 50 + 200 10 10 No damage 100 + 200 10 10 No damage

As shown in Test Example 4, excellent herbicidal effects were provided in the areas treated with the compositions of the present invention. In addition, no damage was found in tomatoes.

Test Example 5

Plastic jars 17 cm wide, 12 cm deep, and 7 cm high, respectively, were filled with field soil, and then cucumbers were transplanted, and dolphins, crow paper, and purslane were planted. The next day, emulsifiable concentrate containing twinomixazine WDG (water dispersible granules containing 51% flumioxazine, trade name: Valor SX, manufactured by Valent U.S.) and a compound of formula (Twin) A mixture of 20 (surfactant, prepared by dissolving a compound of formula 1 in acetone containing sorbitan monolaurate polyglycol ether) was diluted with a predetermined amount of water and applied evenly to the surface of the soil with a small sprayer. .

Treated plants were grown in greenhouses. Herbicidal activity and damage to vegetables were tested 21 days after application. The results are shown in Table 5.

Test compound
Amount of active ingredient
(g / ha) Herbicide activity Weak against vegetables Dolphin Crow Paper purslane cucumber Flumi Jade Photo
+ Compound of formula 1

25 + 50 10 10 10 No damage 50 + 50 9 10 10 No damage 25 + 100 10 10 10 No damage 50 + 100 10 10 10 No damage 25 + 200 10 10 10 No damage 50 + 200 10 10 10 No damage

As shown in Test Example 5, excellent herbicidal effects were provided in the areas treated with the compositions of the present invention. In addition, no damage was found in cucumbers.

Test Example 6

Plastic jars, 21 cm in diameter and 20 cm in height, were filled with field soil, and then the potatoes were transplanted, and the peels, seeds, and morning glory were planted. The following day, the flumioxazine granules (0.25% flumioxazine containing granules, trade name: Broad Star, manufactured by Valent U. S.), granules containing 0.9% of the compound of formula 1 on the surface of the soil of the plastic complex (Prepared according to Formulation Example 9) and a mixture of flumioxazine granules and granules containing a compound of formula 1 were applied manually in the amounts shown in Table 6.

Herbicidal activity and damage to vegetables were tested 14 days after application. The results are shown in Table 6.

Test compound
Amount of active ingredient (g / ha) Herbicide activity Weak against vegetables Dolphin wire grass American morning glory potato Flumi Jade Photo 25 One 5 One No damage The compound of formula (1) 100 0 5 One No damage Flumioxazine + Compound of Formula 1 25 + 100 8 10 7 No damage

As shown in Test Example 6, excellent herbicidal activity was synergistically provided in the areas treated with the compositions of the present invention. In addition, no damage was found in potatoes.

Test Example 7

Plastic jars about 46 cm wide, about 31 cm deep, and about 26 cm high were filled with field soil, and then grapes (variety: Delaware) were transplanted, followed by planting peels, leeks, and hairy snails. Granules containing flumioxazine granules (0.25% flumioxazine containing granules, trade name: Broad Star, manufactured by Valent U.S.) and 0.9% of the compound of formula 1 on the surface of the soil of the plastic complex. The mixture of (prepared according to example 9) was applied manually in the desired amount.

Herbicidal activity and weakness against grapes were tested 14 days after application. The results are shown in Table 7.

Test compound
Amount of active ingredient (g / ha) Herbicide activity Weak against grapes Dolphin wire grass Hairy bean grape Flumioxazine + Compound of Formula 1 200 + 50 10 10 10 No damage

As shown in Test Example 7, excellent herbicidal activity was provided in the areas treated with the compositions of the present invention. In addition, no damage was found in the grapes.

Test Example 8

Plastic jars about 46 cm wide, about 31 cm deep, and about 26 cm high were filled with field soil, followed by transplanting chestnut (breed: long Gin-yose), followed by planting scallops, leeks, and hairy snails. Granules containing flumioxazine granules (0.25% flumioxazine containing granules, trade name: Broad Star, manufactured by Valent U.S.) and 0.9% of the compound of formula 1 on the surface of the soil of the plastic complex. The mixture of (prepared according to example 9) was applied manually in the desired amount.

Herbicidal activity and weakness against chestnuts were tested 14 days after application. The results are shown in Table 8.

Test compound
Amount of active ingredient (g / ha) Herbicide activity Weak about night Dolphin wire grass Hairy bean night Flumioxazine + Compound of Formula 1 40 + 200 10 10 10 No damage

As shown in Test Example 8, good herbicidal activity was provided in the areas treated with the compositions of the present invention. In addition, no damage was found at night.

The present invention enables to suppress various weeds at low doses in farmland, vegetable gardens, trees, non-cultivated land and the like.

Claims (9)

As active ingredient, N- (7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxadin-6-yl) cyclohex-1 A herbicidal composition comprising n-1,2-dicarboxamide (flumioxazine) and a compound of formula 1 in a weight ratio of 1: 0.2 to 1:10. Formula 1

delete delete N- (7-fluoro-3,4-dihydro-3-oxo-4-prop-2-ynyl-2H-1,4-benzoxadin-6-yl) cyclohex-1-ene-1 A method of inhibiting weeds, comprising applying, 2-dicarboxamide and a compound of formula 1 to the weeds jointly or simultaneously to the weeds or to the soil where weeds will grow or grow. Formula 1

delete delete The method of suppressing weeds according to claim 4, wherein the weeds are present in farmland, vegetable gardens, trees or non-cultivated land. The method for suppressing weeds according to claim 4, wherein the weeds are present in farmland. The method for suppressing weeds according to claim 4, wherein the weeds are present in a wheat field.